2-Furancarboxylic acid → 2-Butoxyethylfuroate

HRID 426572Notes

Reaction equation

HRID 426572 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](O)=[O:15].CCCCCCCC(O[Sn](OC(CCCCCCC)=O)(CCCC)CCCC)=O>C1(C)C(C)=CC=CC=1>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:14]([C:10]1[O:9][CH:13]=[CH:12][CH:11]=1)=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 81332-ButoxyethanolHCID 16683953Dibutyltin dioctanoate

Product 1

HCID 867366592-Butoxyethylfuroate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Butoxyethanol (butyl cellosolve) 121 g (1.02 m), furoic acid 95 g (0.85 m) and 1 g dibutyltin dioctoate were heated with a xylene azeotrope to acid number 3. Xylene removed by distillation to a pot temperature of 200° and reaction product distilled. 2-Butoxyethylfuroate collected in fraction 2, 111°-104°. Yield 162 g, 86%.

Workup

  1. customXylene removed by distillation to a pot temperature of 200° and reaction product
  2. distillationdistilled
  3. custom2-Butoxyethylfuroate collected in fraction 2, 111°-104°

Sources & evidence

ORD record
ord-a6942e00bb424faf850a7066f166f3c6
Source dataset
uspto-grants-1979_10
Patent number
US04170584

Reaction notes

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